I provide a close analysis of truth and freedom in Heidegger’s work during the passage from Being and Time (Sein und Zeit) in 1927 to the Contributions to Philosophy (Beiträge zur Philosophie) in 1938. This analysis demonstrates the passage from a Kantian style transcendental analysis of the self to an Idealist inspired study of being-historical thinking. Throughout this shift in thinking, the work of Friedrich Wilhelm Joseph von Schelling is shown to play an increasingly decisive role in Heidegger’s thought, finally leading him to an understanding of the self in terms of freedom, community, culture, and history that carries important implications for political philosophy.